Residents had their say on the proposed £90m Friarsgate redevelopment at Monday night's Winchester Town Forum and it was clear several were concerned it might look like another version of The Brooks.
The modern appearance of the shopping centre reflected badly on Winchester, they said, and hoped planners would not make the same mistake with Friarsgate.
Around 100 people listened to a presentation by city council director of development services, Steve Bee, at the Guildhall, after which council members and residents raised concerns about parking problems, architecture, noise pollution and lack of community facilities.
Current plans for the land between Friarsgate and The Broadway would provide new shops, over 100 flats and a replacement bus station.
"Everyone should know what is proposed, why, and what are the implications. We're talking about roughly trebling the retail in this area. although in terms of Winchester as a whole, this isn't a huge amount.
"Trying to shoehorn a major development into a medieval city like Winchester is no mean feat," said Mr Bee.
Lib-Dem councillor, Ray Pearce, who chairs the forum, added: "It's quite a unique development as it's one of the biggest that will have been built in the city for many decades."
Some residents were worried that the new development might contain a night club. Keith Story, a resident of St Cross, said: "I would like to think this will be a quiet place after midnight and not a place of nightclubs and casinos."
He added he was worried about the architecture "becoming exciting".
Mr Bee said the council had not received any applications for a nightclub at Friarsgate.
He added: "I do not think this is the place for exciting or radical architecture."
Residents also raised fears about parking, feeling there was nowhere to drop elderly relatives at the new bus station. Mr Bee acknowledged it could be a problem, but said there would be spaces nearby at the Friarsgate multi-storey car park.
Labour member, Chris Pines, said it was vital the scheme included a reasonable amount of social housing. "I for one am going to keep the city to account on the amount of affordable homes we have on this site.
"I also think it's important as this is a five-acre development we have some community facilities, like a small museum or library."
The Friarsgate consultation phase ended on Wednesday.
The scheme will be discussed by the city council cabinet in May, after the local elections, and by the full council in June.
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